Dimethylformamide → HCID 57570943, compound

HRID 1695324Notes

Reaction equation

HRID 1695324 reaction equation
[CH:1]([N:4](CC)[CH:5]([CH3:7])C)(C)[CH3:2].[CH3:10][C:11]([S:18][S:19][CH3:20])([CH3:17])[CH2:12][CH2:13][C:14]([OH:16])=O.C(N=[C:25]=[N:26][CH:27]([CH3:29])[CH3:28])(C)C.[OH2:30].O[N:32]1[C:36]2[CH:37]=[CH:38][CH:39]=[CH:40]C=2N=N1.CN(C)[CH:43]=[O:44]>>[CH3:17][C:11]([S:18][S:19][CH3:20])([CH3:10])[CH2:12][CH2:13][C:14]([N:4]1[CH2:5][CH2:7][N:32]([CH2:36][CH2:37][CH2:38][C:39]2[CH:40]=[C:25]([CH2:43][OH:44])[N:26]=[C:27]([CH2:28][OH:30])[CH:29]=2)[CH2:2][CH2:1]1)=[O:16]

Participants

6

Reactant 5

HCID 6228DimethylformamideHCID 12734DiisopropylcarbodiimideHCID 81531DiisopropylethylamineHCID 27960291-Hydroxybenzotriazole hydrateHCID 115646344-Methyl-4-(methyldisulfanyl)pentanoic acid

Product 1

HCID 57570943HCID 57570943, compound

Procedure

To a solution of a sample of the previous residue (160 mg) in dimethylformamide (2.5 mL) was added N,N-diisopropylethylamine (181 μL), 4-methyl-4-methyldisulfanyl-pentanoic acid (158 mg), N,N′-diisopropyl-carbodiimide (88 μL) and 1-hydroxybenzotriazole hydrate (15 mg). After 15 h at room temperature, solids were filtered off and the dimethylformamide solution was injected for HPLC purification according to method F. The appropriate fractions were combined and concentrated by freeze-drying to afford 4-(3-[4-(4-methyl-4-methyldisulfanyl-pentanoyl)-piperazin-1-yl]-propyl)-2,6-bis-(hydroxymethyl)-pyridine (105 mg):

Workup

  1. filtrationsolids were filtered off
  2. customthe dimethylformamide solution was injected for HPLC purification
  3. concentrationconcentrated
  4. customby freeze-drying

Sources & evidence

ORD record
ord-c7f2f51dd1724ac9a7eb41a30a5651c5
Source dataset
uspto-grants-2012_04
Patent number
US08163736B2

Reaction notes

Loading…